CA2475011C - Method for analysis of compounds with amino group and analytical reagent therefor - Google Patents
Method for analysis of compounds with amino group and analytical reagent therefor Download PDFInfo
- Publication number
- CA2475011C CA2475011C CA2475011A CA2475011A CA2475011C CA 2475011 C CA2475011 C CA 2475011C CA 2475011 A CA2475011 A CA 2475011A CA 2475011 A CA2475011 A CA 2475011A CA 2475011 C CA2475011 C CA 2475011C
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- carbamate
- reagent
- amino group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000003277 amino group Chemical group 0.000 title claims abstract description 99
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- 238000004949 mass spectrometry Methods 0.000 claims abstract description 29
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
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- 235000013930 proline Nutrition 0.000 description 1
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- 238000011002 quantification Methods 0.000 description 1
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- 230000002285 radioactive effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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Classifications
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- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6806—Determination of free amino acids
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/15—Non-radioactive isotope labels, e.g. for detection by mass spectrometry
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2560/00—Chemical aspects of mass spectrometric analysis of biological material
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/13—Tracers or tags
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Physics & Mathematics (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pathology (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
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- Analytical Chemistry (AREA)
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- General Physics & Mathematics (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Bioinformatics & Computational Biology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002-36446 | 2002-02-14 | ||
| JP2002036446 | 2002-02-14 | ||
| PCT/JP2003/001463 WO2003069328A1 (en) | 2002-02-14 | 2003-02-13 | Method of analyzing aminofunctional compound and analytical reagent |
Publications (2)
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| CA2475011A1 CA2475011A1 (en) | 2003-08-21 |
| CA2475011C true CA2475011C (en) | 2015-07-07 |
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| CA2475011A Expired - Lifetime CA2475011C (en) | 2002-02-14 | 2003-02-13 | Method for analysis of compounds with amino group and analytical reagent therefor |
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| Country | Link |
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| US (3) | US7148069B2 (enExample) |
| EP (3) | EP2336763A1 (enExample) |
| JP (6) | JP4453363B2 (enExample) |
| AU (1) | AU2003211941A1 (enExample) |
| CA (1) | CA2475011C (enExample) |
| WO (1) | WO2003069328A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2336763A1 (en) | 2002-02-14 | 2011-06-22 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent thereof |
| US20050014279A1 (en) * | 2003-07-14 | 2005-01-20 | Nguyen Hoa Duc | Method of analysis of amine by mass spectrometry |
| EP1686372A4 (en) * | 2003-11-21 | 2009-04-01 | Eisai R&D Man Co Ltd | QUANTIFICATION METHOD USING AN ISOTOPE-MARKED INTERNAL CALIBRATION, ANALYSIS SYSTEM FOR EXECUTING THE QUANTIFICATION METHOD AND ASSOCIATED SEPARATION PROGRAM |
| US20070054345A1 (en) * | 2004-05-19 | 2007-03-08 | Hunter Christie L | Expression quantification using mass spectrometry |
| US20080206737A1 (en) * | 2004-05-19 | 2008-08-28 | Hunter Christie L | Expression quantification using mass spectrometry |
| EP1750126B1 (en) * | 2004-05-26 | 2015-09-16 | Ajinomoto Co., Inc. | Method and apparatus for analyzing aminofunctional compound |
| EP1776588A1 (en) * | 2004-07-12 | 2007-04-25 | Applera Corporation | Mass tags for quantitative analyses |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| US8969089B2 (en) | 2004-10-12 | 2015-03-03 | Quest Diagnostics Investments, Inc. | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| JP2007163423A (ja) * | 2005-12-16 | 2007-06-28 | Ajinomoto Co Inc | 質量分析計によるアミノ酸分析方法 |
| EP1982991A4 (en) * | 2006-02-08 | 2009-10-21 | Nec Corp | PROCESS FOR MODIFYING PEPTIDE AND METHOD FOR IDENTIFYING PEPTIDE |
| JP4771296B2 (ja) * | 2006-02-08 | 2011-09-14 | 日本電気株式会社 | ペプチドのｃ末端のペプチド結合を切断する方法、及びペプチドのｃ末端アミノ酸配列の決定方法 |
| US12367163B2 (en) | 2007-06-29 | 2025-07-22 | Quest Diagnostics Investments Llc | Analysis of amino acids in body fluid by liquid chromatography—mass spectrometry |
| CA2691974C (en) * | 2007-06-29 | 2016-08-30 | Quest Diagnostics Investments Incorporated | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| WO2009054350A1 (ja) | 2007-10-25 | 2009-04-30 | Ajinomoto Co., Inc. | 耐糖能異常の評価方法 |
| US20100285593A1 (en) * | 2007-11-26 | 2010-11-11 | Waters Technologies Corporation | Internal standards and methods for use in quantitatively measuring analytes in a sample |
| WO2009100155A1 (en) * | 2008-02-04 | 2009-08-13 | Prozyme, Inc. | Compounds and methods for rapid labeling of n-glycans |
| DE102009060102A1 (de) * | 2009-12-21 | 2011-06-22 | Martin-Luther-Universität Halle-Wittenberg, 06108 | Derivatisierungsreagenzien zur tandem-massenspektrometrischen Quantifizierung von Proteinen |
| CN106226527B (zh) | 2011-07-21 | 2018-05-04 | 和光纯药工业株式会社 | 血浆中氨基酸分析用内标液、内标物质及血浆中氨基酸的定量方法 |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| JP6193237B2 (ja) | 2011-09-28 | 2017-09-06 | ウオーターズ・テクノロジーズ・コーポレイシヨン | 強められたｍｓ信号を有するグリカンおよび他の生体分子の迅速蛍光タグ付け |
| US10436790B2 (en) | 2011-09-28 | 2019-10-08 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| EP2783388A4 (en) | 2011-11-23 | 2015-12-09 | Quest Diagnostics Invest Inc | DETECTION OF KISSPEPTIN-54 BY TANDEM MASS SPECTROMETRY |
| JP6269502B2 (ja) | 2012-11-27 | 2018-01-31 | 味の素株式会社 | 膵臓癌の評価方法、膵臓癌評価装置、膵臓癌評価方法、膵臓癌評価プログラム、膵臓癌評価システムおよび端末装置 |
| DK3748340T3 (da) | 2014-10-30 | 2022-04-19 | Waters Technologies Corp | Fremgangsmåder til hurtig præparering af mærkede glykosylaminer og til analyse af glykosylerede biomolekyler, som fremstiller samme |
| CN115536714B (zh) | 2014-11-13 | 2026-04-24 | 沃特世科技公司 | 快速标记的n-聚糖的液相色谱校准方法 |
| KR101627841B1 (ko) | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| EP3786619B1 (en) | 2015-05-29 | 2022-06-22 | Agilent Technologies, Inc. | Compounds for labeling amine-containing compounds, and their use |
| CN105548432A (zh) * | 2015-12-18 | 2016-05-04 | 乐普药业股份有限公司 | 一种比伐卢定中氨基酸的检测分析方法 |
| CN109154604B (zh) | 2016-04-24 | 2023-07-21 | 沃特世科技公司 | 用于对用两亲强碱性部分改性的聚糖进行分析的带电表面反相色谱材料方法 |
| EP3472621A4 (en) | 2016-06-21 | 2020-03-04 | Waters Technologies Corporation | Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties |
| EP3472132A4 (en) | 2016-06-21 | 2020-01-15 | Waters Technologies Corporation | FLUORESCENCE LABELING OF GLYCANS AND OTHER BIOMOLECULES BY REDUCING AMINATION FOR IMPROVED MASS SPECTROMETRY SIGNALS |
| PL3480599T3 (pl) | 2016-06-30 | 2025-01-13 | Ajinomoto Co., Inc. | Sposób oceniania ketozy poporodowej |
| CN114839302A (zh) | 2016-07-01 | 2022-08-02 | 沃特世科技公司 | 使用分子量截留过滤和过滤器上去糖基化从复杂基质快速制备标记的葡基胺的方法 |
| US20180094293A1 (en) | 2016-10-03 | 2018-04-05 | Waters Technologies Corporation | Labeled glycan amino acid complexes useful in lc-ms analysis and methods of making the same |
| CN111316105B (zh) * | 2017-09-08 | 2023-10-17 | 豪夫迈·罗氏有限公司 | 用于质谱法的基于亚砜的试剂 |
| JP7151723B2 (ja) | 2017-12-28 | 2022-10-12 | 味の素株式会社 | 給餌管理システムおよび給餌管理方法 |
| KR20250079925A (ko) | 2018-09-26 | 2025-06-04 | 아지노모토 가부시키가이샤 | 경도 인지 장애의 평가 방법, 산출 방법, 평가 장치, 산출 장치, 평가 프로그램, 산출 프로그램, 기록 매체, 평가 시스템 및 단말 장치 |
| CN116773710A (zh) * | 2021-07-13 | 2023-09-19 | 清华大学 | 一种覆盖多种代谢物的代谢组和代谢流的试剂盒和使用方法 |
| CN114354801B (zh) * | 2021-12-31 | 2023-07-18 | 山东大学 | （R）-3-Boc-氨基哌啶中三种氨基吡啶异构体含量的分析方法 |
| CN115925614B (zh) * | 2022-12-02 | 2024-03-08 | 中山大学 | 用于发现可与醛基反应的活性物质的小分子探针 |
| EP4702837A1 (en) | 2023-04-28 | 2026-03-04 | Ajinomoto Co., Inc. | Method for evaluating metabolic disease following calving |
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| JPS5855754A (ja) | 1981-09-30 | 1983-04-02 | Hitachi Ltd | アミノ酸分析方法 |
| JPS6444848A (en) | 1987-08-14 | 1989-02-17 | Hitachi Ltd | Analysis of amino acid |
| US5296599A (en) * | 1991-09-19 | 1994-03-22 | Millipore Corporation | Activated carbamates compounds |
| WO1996002003A1 (en) * | 1994-07-08 | 1996-01-25 | City Of Hope | N-terminal protein sequencing reagents and methods which form amino acid derivatives |
| JP3346965B2 (ja) | 1995-09-14 | 2002-11-18 | 株式会社日立製作所 | アミノ酸分析装置 |
| TW358097B (en) * | 1996-05-24 | 1999-05-11 | Hoffmann La Roche | Beta-lactams and their process and pharmaceutical compositions |
| JP4085443B2 (ja) | 1997-05-07 | 2008-05-14 | 株式会社島津製作所 | アミノ酸の分析試薬及びアミノ酸の分析方法 |
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| EP1329513B1 (en) * | 1998-08-25 | 2011-12-07 | University of Washington | Rapid quantitative analysis of proteins or protein function in complex mixtures |
| GB9821393D0 (en) | 1998-10-01 | 1998-11-25 | Brax Genomics Ltd | Protein profiling 2 |
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| JP4505905B2 (ja) | 1999-11-22 | 2010-07-21 | 住友化学株式会社 | ペプチドのアミノ酸配列決定方法 |
| JP3341041B2 (ja) * | 2000-02-23 | 2002-11-05 | 独立行政法人産業技術総合研究所 | ペプチドのアミノ酸配列解析方法 |
| AUPQ664300A0 (en) * | 2000-04-03 | 2000-05-04 | Proteome Systems Ltd | Macromolecule detection |
| US6716634B1 (en) * | 2000-05-31 | 2004-04-06 | Agilent Technologies, Inc. | Increasing ionization efficiency in mass spectrometry |
| WO2002004936A1 (fr) * | 2000-07-11 | 2002-01-17 | Japan Science And Technology Corporation | Sonde pour spectrometrie de masse d'un echantillon liquide |
| US20060141632A1 (en) | 2000-07-25 | 2006-06-29 | The Procter & Gamble Co. | New methods and kits for sequencing polypeptides |
| JP3508710B2 (ja) | 2000-09-01 | 2004-03-22 | 株式会社日立製作所 | アミノ酸分析方法および装置 |
| AU4338502A (en) * | 2000-10-23 | 2002-06-24 | Genetics Inst | Acid-labile isotope-coded extractant (alice) and its use in quantitative mass spectrometric analysis of protein mixtures |
| CA2426728A1 (en) * | 2000-10-23 | 2002-06-13 | Genetics Institute, Llc. | Isotope-coded ionization-enhancing reagents (icier) for high-throughput protein identification and quantitation using matrix-assisted laser desorption ionization mass spectrometry |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US6818454B2 (en) * | 2001-02-16 | 2004-11-16 | Battelle Memorial Institute | Phosphoprotein binding agents and methods of their use |
| JP3464665B2 (ja) | 2002-01-07 | 2003-11-10 | 株式会社日立製作所 | アミノ酸分析装置 |
| EP2336763A1 (en) | 2002-02-14 | 2011-06-22 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent thereof |
| EP1750126B1 (en) * | 2004-05-26 | 2015-09-16 | Ajinomoto Co., Inc. | Method and apparatus for analyzing aminofunctional compound |
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| US9658234B2 (en) | 2017-05-23 |
| EP1475632B1 (en) | 2013-05-22 |
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| JP6699645B2 (ja) | 2020-05-27 |
| EP1475632A4 (en) | 2008-06-25 |
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| JP2013015537A (ja) | 2013-01-24 |
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| JP2020073916A (ja) | 2020-05-14 |
| EP2317307B1 (en) | 2013-11-20 |
| WO2003069328A1 (en) | 2003-08-21 |
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| AU2003211941A1 (en) | 2003-09-04 |
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